Hellbound
by Mockingfire
Summary: What if Dean never escaped Hell? The angel's rescue mission was compromised. Castiel was taken as Hell's prisoner and after years of torture Dean gives in to the darkness and becomes the very thing he hates. A Demon. (sort of au, but follows the events leading up to season 10)
1. Chapter 1

_**Hey guys, so while re-watching some episodes with my sister, I had an idea, what if Dean never actually escaped from Hell, what if Cas's rescue mission went wrong. he dreams Dean had after escaping Hell, what if they were reality and Dean only imagined getting out and all of the events that followed, well given the season 9 finale, it seems that whether Dean got out or not, the outcome is the same (if you haven't seen season 9 please don't read on!)**_

_**anyways I hope you enjoy! (and if anything doesn't make sense please just ask, though the next chapter should clear up any questions :) )**_

_**amber xx**_

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Hell was just as bad as Deans worst nightmares; each and every one of his fears rolled up into one. It wasn't the torture that got to him- he could deal with pain, he had a fair bit of experience with it. It wasn't the realisation that he would never see the people he loved again that tore a chasm in his chest. It wasn't even that he was on a one way path to becoming one of the monsters he'd spent his whole life fighting to kill...

No. it was the fact that there was nothing he could do about it. He was helpless. He was fighting a battle he had already lost and he knew it, but God knew he wasn't going to go down without a fight.

Every day passed the same as the last. They would slice and tear at him, slowly, carving away at his skin, savouring every cry of pain like it was a symphony, as they ripped through muscle tissue, sawing bluntly through each individual nerve. agony. As they roughly tore open his ribs ,like wrapping paper, snapping his bones like twigs. Hacking away at him until there was nothing left. Then he'd be whole again and they would start over. An endless cycle of torment.

Screams of agony tore though him almost constantly, but they melded with those of the other damned souls, merging together, amplified. It wasn't that there was noone to hear them scream, it was quite the opposite, there were too many. After a while it become impossible to distinguish his own cries from the others around him. So many souls, so much pain. That's all there was there; Pain.

He discovered that you could still sleep in Hell, but the screams wove through his dreams, shadows and darkness seeping in from every corner of his mind. No rest for the wicked...

Dean learned to identify the different demons as time went by, there was one in particular that stood out from the others, his name was Alistair. He was much stronger than many of the demons he and Sam had fought, he had an air of command about him. And for some reason this demon had taken a particular shine to him. Every day without fail, Alistair would make him an offer, Dean could get off the rack, they would stop the torture, no more pain, if only he would put souls on, if he started the torture. Every time Dean told the black eyed son of a bitch to stick it where the sun don't shine.

After 30 years Dean felt his resolve beginning to waver, he prayed for help, for strength to carry on. He thought once he had heard someone speak to him.

He started hearing things, in his mind. A voice that wasn't his own.

_"Help is coming_" the voice said and he could have sworn he heard the sound of wings, Dean waited and waited, clinging the small hope of rescue while demons slashed and tore at him. But time passed and no help came and Dean eventually passed it off as wishful thinking, there was noone coming, there was no getting out of this place. Maybe he was just losing his mind...maybe he already had...

30 years turned to 40 and Dean was on the verge of giving in, every day Alistair's offer became more and more appealing.

What would it matter if he said yes? He'd be torturing souls, true, but if he didn't do it some demon would do it anyway...

But 40 years into his sentence, Dean started to have dreams. Not like the nightmares he had been plagued with since he first arrived. These were different, far more vivid, almost like memories and something impossible happened, Dean was saved.

Not physically. But in his dreaming moments, He saw himself escape Hell, rescued by angels.

Dean knew it wasn't real, he would wake up and he'd still be on that rack but it _felt_ real and it didn't stop there he saw everything; Angels, demons, the devil, the apocalypse, purgatory, Sam, Bobby, Ellen, Jo...

In those moments, he often found himself wondering where reality truly was, it was almost as though Hell was the dream. If only...

They weren't happy dreams, he watched his friends die over and over. Grief, pain, disappointment, betrayal. No, it wasn't happy, but in his dreams he was alive, if only for a little while and that kept him going, day after day, month after month, year after year after year, he clung to those dreams, to those he loved, they kept him human, they helped endure the torture. No matter how bad the dreams where, he'd have given anything for them to be real, they reminded him of why he was here, why he was still fighting and what it meant to be human.

He grasped the images in his mind, they were his distraction, his anchor to humanity.

There was one person above all who stood out from the others, he was more vivid than anyone, the angel. _His_ angel, Castiel. He was the main reason he carried on fighting as long as he did. Dean had never had a friend like that before, he gave up everything for him. He made Dean feel like he was actually worth something, not just a good little soldier, he didn't have to been someone else, he wasn't just a pawn in someone else's game, he was Dean Winchester with a GHD in Give 'em Hell Attitude. He had people who loved him, needed him, he was a good man...yes they were dreams, maybe his angel wasn't real and he hadn't stopped the apocalypse but that didn't change the fact that he and Sam had saved lives and Dean realised, he was proud of them both, something he never thought he would ever be able to admit.

Unfortunately, not even angels could keep Hell at bay forever. The darkness bided its time, slowly creeping through the shadows of his mind, it's tendrils reaching out to every corner of his thoughts, slowly but surely claiming him for its own.

300 years he tolled but eventually it all just became too much. His dreams became nightmares and he found that sleep no longer offered any solace.

Pain and darkness filled the spaces where his dreams had filled and Dean found himself back where he started, this time was worse, because he realised, there was no point fighting anymore, even in his subconscious there was no escape, fate had caught up with him, there was no where to hide. You can't run from yourself.

So when Alistair asked him for the final time, the victorious glint in the demons eyes said he already knew the answer, he knew he wouldn't be asking again.

'So Dean,what's it going to be, Yes or no?' he smirked.

Dean closed his eyes, taking a final deep breath, he saw himself lying on a bed, lifeless...

'Yes' He said, opening his eyes to meet the demons dark gaze, letting go of his past, staring into his future. And as he did so, one last image flashed across his mind.

In his minds eye, Dean watched his dead body lying on a bed motionless, he knew what was going to happen, it was always going to be the outcome. The motionless figure opened his eyes. Despite fighting against it for so long, Dean always knew this outcome was inevitable.

His eyes were the last thing he saw, the colour of the darkness which surged through every fibre of his being, the colour of his soul.

Black.

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_**Okay so what did you guys think? please let me know :) I've got a least 1 more chapter for this, looking into what happened with the angel's rescue mission, what went wrong, what happened to Cas, why Dean had those dreams and maybe most importantly, what effect they will have on Demon!Dean :D**_

_**Please let me know what you think, I wont bother writing any more if noone's interested, I hope you are because the next chapters going to be interesting ;)**_

_**If you are one of my tumblr followers and you don't have an account leave a review under your tumblr name and I'll make sure to tell you when I update! :)**_

_**Thank you all for reading! **_

_**Amber xx**_


	2. Chapter 2

_**Hey guys here's chapter 2 a bit more insight into Demon Dean :) (sorry for any mistakes i'll fix them tomorrow :P)**_

_**i'm too tired to write a long note so just a quick thank you to**__bayreaper _**_for your review _**

**I hope you enjoy this, please let me know what you think in the review box :)**

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**Hellbound Chapter 2**

Dean adapted to his new life almost too easily. He excelled in every aspect, but nothing more than when it came to torture. Saying he was good at it, was like saying that Hell was a little gloomy; the understatement of the century. Alistair took him under his charge, assuming the title of 'mentor' though Dean thought prison warden was more accurate, because while Dean had escaped the chains, his hatred of demons had never once faltered.

Dean knew that the other Demons didn't trust him as far as they could spit, he had made it his life's mission to destroy as many of them as possible, many of them had personal reasons to hate him and he knew they would never accept him as one of them, there was something different about him though, compared to the other demons, besides the difference in genetic code unlike the others he still remembered what it was like to feel, to be human. He didn't know why, maybe it was something that would disappear over time.

Either way, it didn't matter to him, he didn't belong there and he never would because while Dean may have gone along with Alistair's tuition, putting on the face of cooperation, he would just as rather turn the blades on Alistair and the other demons as on the souls awaiting retribution, that is if there were any chance of survival if he tried.

So instead Dean played along, he was a good little demon, following the rules doing as he was told, all the while playing by his own rules. He found after a while he began the enjoy himself. Torturing souls brought him an acute sense of satisfaction, he found himself mesmerized by the way crimson seeped from beneath the blade of a knife, the way the skin spit, giving with almost no pressure, so delicate, so breakable. Bones, so fragile they snapped with little effort on his part.

Dean knew that if his human self could see him now, he would be disgusted, but that was the thing about being a demon, he didn't care, he had no guilt and for the first time in his existence, he he had control of the reigns, the weight of responsibility had been lifted and Dean didn't have to think about anything other than himself, he didn't to worry about saving people or watching out for Sammy, for once he had control, he felt alive. He didn't miss being human, though he did find himself wishing that he could still dream, but of course demons didn't sleep and they didn't dream.

Dean slipped into the new lifestyle, as content as one could be while living in Hell. The routine remained almost the same until one day, Alistair said he had a 'special job' for him, a prisoner needed a little encouragement to find his tongue.

Dean followed Alistair into the cell, Dean's step faltered when he saw the prisoner in question.

Alistair frowned 'you know this angel?'

'angel...' Dean repeated then realising Dean shook his head quickly. 'no, never seen him before in my life' which was technically true, he had never seen him before he had died. 'I thought...he reminded me of someone I guess' He said, Alistair didn't look convinced, but shrugged it off.

'What's he doing here?' Dean asked.

'Well, our little guest here was caught trying to sneak in with some of his buddies.' Alistair smirked. 'We soon put a stop to their little vacation.'

'What?' Dean shot a look towards the strung up angel. 'why the hell would they want to break in here?'

Alistair stared hard at the prisoner 'That's what we'd like to know, but this one seems to be having some trouble finding his voice.'

'What happened to the others? The ones with him?' though Dean was sure he already knew the answer.

'dead.'

'I thought we'd see if you could make him squeal.'

Dean stared at the limp figure.

'That is' Alistair said. 'If you're up for the challenge. If not we can always find you a nice easy soul to break...'

'I'll do it.' Dean cut in.

'Good boy. Let's see how persuasive you can be.'

'I'll be back to check on your progress later. Make sure you have something to show or I'll have to rethink this promotion of yours.'

Alistair left, leaving Dean alone with the angel.

Dean looked at the table laden with tools, an array of sharp objects with only one purpose. Pain.

Selecting a scalpel, Dean passed it between his hands, testing the feel of it against his palm. Slowly he walked towards the prisoner ready to make him talk.

But as Dean raised the blade to make the first incision, the angel lifted his head, and their gazes met.

Dean stared into the deep blue eyes suddenly finding himself frozen, unable to look away. This wasn't compulsion, at that moment he was struck with memories. Emotion flooded him and all of a sudden the cold metal of the scalpel felt foreign in his hand and a moment later it slipped from his grasp, the clattering loudly as it hit the stone below.

'Cas...?' name he had never spoken aloud, only in his mind, in dreams.

'Hello Dean' his voice was weak, barely audible, but it struck something deep inside him. This was real. He was real. Somehow his dreams had been real...

'What the hell are you doing here?'

The angel didn't answer just looked at him with a sadly, reaffirming what he'd already known deep down.

'No.' Dean shook his head 'You stupid son of a bitch.'

He searched the angels expression for another explanation.

'Tell me you didn't get yourself into this mess for me.' No response.

'Damn it Cas, you should have just left me...' Dean shook his head.

The angel looked as if he was trying to argue, but he flinched in pain.

'You don't have to say anything. You have a hell of a lot of explaining to do mind, but right now all that matters is getting you out of here.'

Dean glanced around,

'Question is, how?...I can't even zap myself outta here, never mind the both of us. We need help but I don't know anyone, they'd all rather tear me apart than than help me out...'

Cas mumbled something,

'What?' Dean said.

Cas tried again but no sound left his lips, giving up any further attempts, Dean heard a single word in his mind.

_Crowley_ the word rang clearly, though Dean knew it had taken a great deal of energy, which Cas didn't have.

'Crowley' Dean repeated aloud. 'King of Hell, Crowley?'

Cas didn't respond but almost as soon as Dean had spoken a figure stepped out of the shadows.

'It's king of the crossroads, you moron-' a voice from behind him said, Dean spun to face the new arrival only to find himself facing another familiar figure.

'-though, I like the way you think. Does have a nice ring to it; King of hell' The demon shrugged then continued.

'Dean Winchester, you took your sweet time.'

'You?' Dean said.

'Me' Crowley said. 'We'll have time for formal introductions later boys. First we need to get you as far away as possible, before someone notices you're gone or worse finds me helping you.'

'Why would you help us?' Dean questioned.

"Let's just say I have my reasons and leave it at that. If you think you can bust out without my assistance be my guest." finally Dean nodded. "Fine."

Dean bent down and pried open the manacles around Cas's ankles and wrists. As Dean freed the angels hands, Cas slumped forward and Dean caught him. Supporting his weight Dean turned back to Crowley.

'So how exactly do you suggest we get out' Dean asked, 'This is Hell'

'Aren't you the clever one.' Crowley rolled his eyes. Then pointed at the ground like he was talking to an infant.

'Hell' then pointed a finger at himself 'demon'

And without another word Crowley placed a hand on Deans arm and clicked his fingers.

'Where are we?' Dean asked looking about.

'Wyoming' Crowley said vaguely.

'We're back on earth.' Dean marveled taking in his surroundings. It was as though they were in the centre of a meteorite crater. It had to be half a mile in radius, at least. An expanse of dust, fallen trees and charred debris, completely flattened. It looked like the area had been nuked.

Dean shifted his hold on Cas who had lost consciousness. It was then that Dean noticed something else.

Close to where they were standing.

A cross, formed out of two pieces of wood, lopsided, and it was then it struck him. He'd been here before. Almost exactly like this. Except last time he had crawled out from the ground. This was his grave.

Dean glanced down at himself at that moment and noted something else.

'How do I look like this?' he asked. 'My body was destroyed. Torn to shreds and anyway it's been buried for long enough that it'd be worm chow years ago.'

'Consider it a gift.' Crowley shrugged. "Him too." he indicated to the angel "he was very specific about the vessel." Dean noted the dark hair and trench coat, and knew that the eyes behind his closed eyelids were a piercing blue.

'Wait how long has it been?' Dean asked

'Earth time, about seven years give or take.'

'Seven years...What about Sam?' Dean said suddenly.

'What about him?' Crowley asked.

'Is he alive?' Dean demanded.

The crossroads demon shrugged. 'He hasn't made an appearance down below so it looks like your deal paid off.'

'Where is he?'

Crowley sighed. 'What is this fixation with you two? I don't know, and I don't much care. He went off the radar a good few years back, no idea how he did it. My guess is he found himself an angel.'

Cas stirred slightly then went limp again.

'We need to get him somewhere safe.' Dean told Crowley, who raised an eyebrow in amusement.

'Do I look like your mother? You're on your own from here, I've stuck my neck out enough getting you two idiots this far. I've got to get back before they notice anythings wrong.'

Dean scowled, then said 'Well, thanks for getting us this far I guess.'

'Yes well, just don't make me regret this. Fix what needs fixing.'

And with that he disappeared, leaving them alone.

'Great, so looks like we're on our own.' Dean muttered, then chucked dryly.

'We're a right pair.' Dean told the insentient figure.

'A Hell's school dropout and Mr comatose .' Dean paused, a sense of déjà vu washed over him. He shook his head to shake the feeling.

'Yeah, we'd strike fear into the hearts of our enemies.' Dean smirked, glancing around.

Not sure exactly where he should go, Dean hoisted the unconscious angel over his shoulder and set off walking in the direction of what looked like a road in the distance, hoping they didn't run into any unfriendly company.

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_**So there we go, chapter 2, what'd you think? **_

_**(and yes, they did appear in the same place as season 4 ep 1)**_

_**if you like it so far make sure you follow to be told when I update**_

_**coming up, Dean and Cas talk and Sam finds out that Dean's back and you'll meet Sam's Angel Friend :D **_


	3. Chapter 3

_**Hey guys! so I've gone back and edited chapters 1 and 2 (finally) and here's chapter 3! still not sure just how long this fic will be, there will definitely be at least 1 more chapter so if you'd like to read more please 'follow' to be told when I update :)**_

**_To everyone who reviewed, favourited or even read the last two chapters thank you so much!_**

**_To Babyreaper -Who are you and how on earth do you review so quickly? Is it coincidence that you happened to be online when I updated or are you a demon? Either way thank you so much for your lovely comments and questions (if you send me a message I can answer any questions for you), In response to your comment about Dean aging, I've briefly mentioned it in this chapter, but to clarify since in the show Dean had aged when he escaped Hell, I decided to stick to that so Dean looks like he does in Season 10 (as Demon Dean) :) and on the subject of him being a 'good demon' I'd say it's not as simple as good/bad, I'll let you decide :)_**

**_anyways, happy reading, let me know what you think :)_**

**_amber xx_**

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Dean followed the dirt track, red dust rising in the wake of his heavy footsteps. Cas, slung unceremoniously over his shoulder, remained unresponsive.

After an hour or so walking, he came across a rundown looking motel, the neon vacancy sign was flickering weakly in the window.

A greasy haired man stood at the reception desk, his concentration fixed on a copy of yesterday's paper. Dean cleared his throat.

"Hey there.." the man said lifting his head, he froze when he saw Dean, then his gaze flickered to Cas's prone figure over his shoulder.

"We're looking for a room." Dean said.

The man looked between the two and frowned, "He alright? Do you need to call a doctor or somethin'?"

"Nah he just drank too much." Dean lied smoothly.

The man still looked sceptical but seemed to decide that he needed the business.

"a'right then...a king or two queens?"

"King'll do just fine." Dean grinned,

"how long'll you be staying with us?"

"not sure yet, a couple nights."

The man nodded then with another concerned look at the angel he asked, "You sure he don't need a doctor?"

Dean shook his head, "We're good." He repeated, more firmly this time.

"Well alrigh' then, yours is room 4, just down the hall. Any problems just give me a holler."

The man reached down behind the desk for a room key, but his elbow knocked a precariously balanced glass of water, which fell from its perch. Water splashed over Dean, stinging where it touched his bare skin.

"Holy water." Dean hissed, "Now that's not very nice." His eyes flickered black.

The man started chanting...  
"Omnus imundus spiritus...omnus satanica portestas... Omnus incursio infernales..." Dean felt a tugging sensation from inside, like his insides were trying to escape, but it didn't do much other than make his step falter.

It took Dean less than a heartbeat to act, he let Cas slide to the ground and the next moment he had the man up against the wall by the throat.

"You know, I didn't want to have to kill you..." The man snorted disbelievingly, or he would have done if Dean hadn't been crushing his windpipe.

"Yeah, unbelievable right?" Dean agreed. "Truth is, I'd just have rather left you alive...but you left me no choice. Can't have you trying to kill me again, can I?" The mans eyes lost their hard expression, replaced by fear.

Dean twisted the man's neck in one swift motion, killing him instantly with a sickening 'snap'. Dean let go and the man fell to the floor lifeless. Dean looked down at the corpse and he felt...nothing. As a second thought Dean took the man's cellphone. Then, he plucked the key from where it was hanging and without another glance he picked up Cas and proceeded to room 4.

Dean paced up an down the room. Cas lay comatose on the bed and Dean wondered if the angel would ever wake.

He caught sight of his reflection in the grimy mirror and marveled, there was no indication that this body had been torn apart. He didn't look all that different from when the Hellhounds had killed him. A little older. Seven years older he presumed. He looked more rugged, his hair a little longer, his features more defined, his jawline more pronounced. But he still looked like himself. There was almost no sign of the darkness that now ran through his veins. Not until his eyes flickered black.

Taking out the cell, he dialed Sam's number.

He'd tried every number he could think of but not surprisingly all of them were disconnected.

There was one last number Dean hadn't tried.

Before Dean's last year was up, Sam picked up a new phone, an old Nokia brick, practically indestructible, and he gave the number to only one other person, Dean.  
It was for just it case. In case Dean managed to get out. Wishful thinking. But Dean knew that Sam would have kept it.

Dean typed in the number but instead of calling he sent a text.

_**Ryden's motel, Wyoming. **_

Then remembering what Crowley'd said he added,

_**Feel free to bring your angel friend. **_

He didn't sign it , in case it fell into the wrong hands, though he'd been dead for the last seven years so it probably didn't matter, you can never be too careful though and Sam would know who it was from when he got it.

If he got it.

With the message sent the only thing left to do was wait.

If was almost sun down when Cas finally came to. Dean had been standing at the window, just watching the day tick by, reveling in the quiet. Thinking about how much everything had changed since he'd last seen the sun...

"Hey, you good?" Dean asked as Cas pulled himself up. The angel slowly stretched his limbs, wincing at the movement.

"I'm alive." Cas said after a moment.

"Well that's something at least." Dean shrugged. "Listen, I wanna say thanks."

Cas frowned, "why?"

"Because you didn't give up on me. I don't know why you'd try and bust me out in the first place, but whatever reason, you didn't give in."

"It was my mission"

"Nah that's a load of crap, sure that was why you came after me, but your friends...family, we're killed and you fought on..."

"I failed..."

"No , you didn't. You saved me."

The angel tilted his head as Dean had seen him do countless times in his mind.

"I can't explain it, I liked torturing those souls. I enjoyed it. I felt strong, powerful, even now thinking about it, I don't feel guilty. I just...satisfaction...it's sick I know, but it's the truth. I never felt like I belonged though. They all hate my guts, even if I am on their side, they saw this as punishment for me. The thing is I still hate them. I'm different from them, somehow. Because I still remember, humanity, I didn't lose that. I know the things I've done, would have disgusted me. I know it but I just don't... Feel it." Dean paused thoughtfully glancing back at his reflection in the mirror. "I never wanted to be this."

"I'm sorry Dean, that I couldn't save you. I failed."

"No Cas, don't you get it? you did save me."

"When I said never wanted this life, what I really meant was I didn't want to be like them. I never knew there was an option, but what I really didn't wan't, was to forget. And because of you, I didn't."

"forget?"

"What it's like to be human. I don't feel...I don't have that connection to them anymore, but I remember how it was, I remember the pain, the fear, but also the good. Those dreams," Dean asked, "we're they real?"

"Not entirely." The angel said frowning as he deliberated how best to explain. "When I was captured I tried to reach out to you, to reassure you, but I couldn't completely break through while you were awake, you're mind was too...preoccupied. I managed to link to your thoughts while you were asleep." He said. "Those images, they were...a possibility. Had the rescue been successful, that is a path you might have followed. However, nothing is certain.

It was the engine Dean heard first. The low rumble of the Impala, the crunch of it's tyres over gravel as it came to a halt. The angel had heard it too and the pair fell silent, listening.

After a few minutes there was the tell-tail squeal of the main door opening, and muffled voices. Dean heard the sound of footsteps coming along the corridor outside the room.

Pressing a finger to his lips, telling Cas to keep quiet, Dean walked to the door.

Slowly Dean opened it, a knife hidden behind his back, just in case.

He came face to face with his younger brother.

'Dean?' Sam stared, a mixture of disbelief and joy shone in his brown eyes.

'Hey Sammy.'

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_**So there you go guys, hope you enjoyed this chapter, I'm not sure when I'll be updating next so if you want to read more please follow or send me your tumblr name so I can tell you when I post a new chapter.**_

_**xx**_


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